Award Winners
The history of the CSSL Awards winners are listed with the information available to the CSSL.
| Year | Personality of the Year | Fairplay Award |
| Heathcote Choc Brown Memorial Trophy | Verberne Trophy | |
| 2024 | Murray Ralfs (Life Member) | Bolei Khan (Babasiga Lions) |
| 2023 | Andreas Cooper (Hoon Hay) | Whakaraupo FC |
| 2022 | Saroj Chauhan (Lhotshampa FC) | Robbie Foulkes (UCAFC Obikwa) |
| 2021 | Ronan Farrelly (Glenbyre) | Thomas Marsh (Coastal Spirit Rovers) |
| 2020 | Sudhir Pawar (Fiji Rovers) | William Walsh (St Albans Squires) |
| 2019 | Peter Cattermole (Glenbyre) | Ryan Kolarikkal (Glenbyre) |
| 2018 | Tommy O’Donahue (Dux de Lux) | Alan Brook (Universities) |
| 2017 | Ben Williams (Glenbyre) | Arran Eady (Alvarados) |
| 2016 | Ben McNabb (Coastal) | Matt Sands (Prebbleton) |
| 2015 | Murray Ralfs (Christchurch United) | Josh Smith (Southern Districts Salamanders) |
| 2014 | Sheridan Cattermole (Glenbyre) | Joe Hitchcock (Alvarados) |
| 2013 | Pat Sloan (St Albans Squires) | Dux de Lux A |
| 2012 | Bevin Jones (Avonhead) | WF Riverside |
| 2011 | Bob Damodran (Avonhead) | Blue Shirts |
| 2010 | Glen Bellam | Dayle Keown |
| 2009 | Glen O’Callaghan | Ilam Hardies |
| 2008 | Sudhir Verma | Nepali Gorkhali |
| 2007 | Shannon Gilmore (Prebbleton) | Paul Stokes |
| 2006 | Barry McTague | Sudhir Verma |
| 2005 | Rob Munro | Prebbleton |
| 2004 | Damien O’Brien | Kamlesh Mani |
| 2003 | Dave Nadan | Gavin Searancke |
| 2002 | John Dyksma | |
| 2001 | Sue Verberne | |
| 2000 | Peter Donnelly | |
| 1999 | Terry Alder | |
| 1998 | Brent Wall | |
| 1997 | Tom Kendall | |
| 1996 | Andy Swarbrick | |
| 1995 | Ray Jones | |
| 1994 | Kevin Cogle | |
| 1993 | Ken Harvey | |
| 1992 | K Tatterson | |
| 1991 | Eric Phillips |
